A fluorine-containing olefin represented by, for example, formula: CnFmXl wherein m+l≤2n and n≥2, and Xs each independently represent F, Br, Cl, I, or H is a useful compound that has applications in various functional materials, solvents, refrigerants, foaming agents, etc., and is also useful as a monomer for functional polymers or as a starting material for a monomer. For example, a fluorine-containing olefin can be used as a monomer for modifying an ethylene-tetrafluoroethylene copolymer.
Fluorine-containing olefins have traditionally been produced by suitably combining a variety of reaction steps, such as fluorination, halogenation, defluorination, dehydrofluorination, dehalogenation, and dehydrohalogenation, using a variety of hydrocarbons and halogen-containing hydrocarbons as starting materials.
It is reported that 2,3,3,3-tetrafluoropropene (HFO-1234yf), which is seen as a promising low-global-warming-potential refrigerant compound, is produced by subjecting a chlorine-containing compound to a combination of reaction steps, such as fluorination, dehalogenation, and dehydrohalogenation (PTL 1). PTL 2 and 3 disclose a method for producing HFO-1234yf by repeating hydrogenation and dehydrofluorination using hexafluoropropene (HFP) as a starting material compound. Moreover, PTL 4 discloses a method for producing HFO-1234yf by catalytically dehydrogenating HFC-254eb and HFC-254fb.
For example, when HFP is used as a starting material compound, HFO-1234yf can be produced through the following reaction steps.CF3CF═CF2(HFP)+H2→CF3CFHCF2H (HFC-236ea)  (1)CF3CFHCF2H→CF3CF═CFH (HFO-1225ye(E/Z))+HF  (2)CF3CF═CFH+H2→CF3CFHCFH2 (HFC-245eb)  (3)CF3CFHCFH2→CF3CF═CH2 (HFO-1234yf)+HF  (4)